Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies

Chiral Phosphoric Acid Directed Regioselective Acetalization of Carbohydrate‐Derived 1,2‐Diols

“…In contrast, functionalization of the C3 position has been observed for the substrate-controlled reactions of the b-d-glucose-derived 2,3-diols. [12] Because of the low solubility of the precursor to 4 b, its reaction with dihydropyran was significantly slower than those leading to 3 a and 4 a, even at 0 8C. While the reaction catalyzed by (R)-2 d provided 4 b (entry 3, C2/C3 = 6:1), the reaction catalyzed by (S)-2 d was sluggish and favored formation of the C3protected isomer (C2/C3 = 1:2.6).…”

Design of a Candida albicans Disaccharide Conjugate Vaccine by Reverse Engineering a Protective Monoclonal Antibody

“…The syntheses of disaccharides modified at the reducing monosaccharide (internal) residue, compounds 2−7, have been described. 25 Syntheses of disaccharide 1 and disaccharides modified at the nonreducing (terminal) mannose 8−15, as well as trisaccharides 16−18, are given in brief outline with full details in the Supporting Information. The synthesis of three trisaccharide congeners 19−21 is reported separately.…”

Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by 19F NMR Spectroscopy

“…As mentioned above, the OH by F substitution has been extensively used in carbohydrate chemistry to map the key hydroxyl groups of a given sugar that are involved in their recognition by lectins, antibodies, transporters, or enzymes. − The methodology presented herein, which employs a rationally assembled collection of monofluorinated monossaccharides for which their hydroxyl groups have been systematically substituted by fluorine atoms, allows dissecting chemical mapping information regarding the importance of each individual hydroxyl group in the interaction with its receptor. For MGL, the same experiment allows identifying its selectivity for Gal moieties and simultaneously shows that hydroxyls at positions 3 and 4 are essential to keep the interaction ability of the Gal analogue, while hydroxyls 2 and 6 can be modified while still maintaining binding to MGL.…”

“…From the molecular recognition perspective, different approaches have been tested to examine the relevance of hydroxyl groups from saccharide units in binding to receptors. One extensively applied approach rests on screening a given set of available closely related saccharides that display different stereochemistry and/or substitutions at a certain site within the sugar ring. − This protocol synthetically eliminates or modifies hydroxyl groups (deoxygenation, methylation, exchange by halogens) . In particular, hydroxyl-by-fluorine substitution has been used to trace key hydroxyl groups for contact with either lectins, antibodies, transporters, or enzymes …”